Hypervalent iodine (V) compounds are known to be useful oxidizing agents for the conversion of primary and secondary alcohols to their corresponding aldehydes and ketones, e.g. De Munari, S. et al, Journal of Organic Chemistry, 1996, 61, pp. 9272-9279. Dess-Martin periodinane (DMP), 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, is often the reagent of choice for the oxidation of primary and secondary alcohols due to mild reaction conditions (room temperature and either slightly acidic or neutral pH) which are especially suitable for substrates which contain sensitive functional groups. However, DMP explodes violently upon heating under confinement (Chemical and Engineering News, Jul. 16, 1990, p. 3). The hazardous explosive properties of DMP make its use on a manufacturing scale prohibitively dangerous.
Therefore, it is an object of this invention to provide a selective and safe oxidation process for the conversion of a primary or secondary alcohol to the corresponding aldehyde or ketone.
It is another object of this invention to provide an oxidation process which affords high product yields.
It is also an object of this invention to provide a composition useful in the process of this invention.
It is a feature of this invention that the oxidizing agent is used in situ, thereby eliminating the need for additional separation or isolation steps.
These and other objects and features of the invention will become more apparent from the detailed description set forth herein below.
The present invention provides a safe and effective process for the selective oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone which process reacting said alcohol with a solution containing an anhydride of the formula (RCO)2O and a trialkanoyl periodinane compound of formula I 
wherein R is C2-C4 alkyl. Preferably, R is ethyl or n-propyl.
The present invention also provides a composition useful in the process of the invention, which composition comprises a solution of an anhydride of the formula (RCO)2O and a trialkanoyl periodinane compound of formula I dissolved in a suitable solvent, e.g., an aromatic hydrocarbon such as toluene.